Transform Your Leadership Retreat

It's that season again—the time for gathering your teams and charting the course for the next 12 months and beyond. The insights you've gained about your business and team over the past year are invaluable, and it's only natural to be excited about integrating these into your upcoming strategy session. But before you set off to your agency's next offsite meeting, armed with sticky notes and tons of ideas, take a moment to consider the key factors that will contribute to a successful meeting. The success of your strategic planning offsite hinges on the clarity and focus you bring into the room. To set you up for success, I've compiled a list of pre-offsite questions. Reflecting on these will assist you in crafting an agenda that aligns your entire team toward a common goal.

I've organized the questions into six major areas to make it easier to decide where to focus your energy. When planning your leadership offsite, choose a topic that resonates with both you and your team. For each topic, I've included questions designed to spark thoughtful discussion. While it may be tempting to cover multiple topics, resist the urge; experience shows that agencies achieve more positive outcomes when they focus on a single area.

Here are the six topical areas to consider for your strategic offsite:

  • Attracting clients

  • Improving client retention

  • Boosting your team's skills

  • Getting more done (without experiencing burnout)

  • Becoming the go-to experts in your field

  • Reducing costs

After selecting your topic, leverage the starter questions below to frame the discussion for your team. These prompts will provide clarity and assist you in articulating your meeting's desired outcomes before the offsite. Don't hesitate to invite a moderator to help facilitate the conversation during the offsite.

Attracting clients

  • What characteristics define our ideal client?

  • How are we currently sourcing leads? Does this strategy fit with our ideal client profile?

  • How might we attract more of our right-fit clients?

Improving client retention

  • Are clients satisfied? How do we know?

  • Have we been losing clients and if so, are there any common denominators?

Boosting your team's skills

  • Can our current team deliver the services we say we can deliver?

  • What are the current skills gap within the team?

Getting more done without burnout

  • Am I the bottleneck in our current work processes?

  • Have we been losing people we wanted to keep and if so, are there any common denominators?

  • How might be leverage technology to improve efficiency?

Becoming the go-to experts in your field

  • If it's not us, then who is it?

  • Are there partnerships or collaborations that could elevate our expertise?

  • What trends should we be aware of?

Reducing costs

  • Should we consider outsourcing or partnerships to reduce operational costs?

  • Have our costs increased relative to sales in the past quarter? past year?

This article is intentionally brief to allow you the space to think, not just read. So, take a moment to consider what you hope to achieve in your upcoming leadership offsite. When you walk into that room, armed not just with compelling presentations and fun snacks but also with insightful questions and unyielding focus, you set the stage for a strategy session with the potential to truly transform your agency. Your preparation will pay off. Now go make some magic happen!

Leadership, StrategyJeff Meade